(E)-3-(3-Chloro­phen­yl)-1-(4-methoxy­phen­yl)prop-2-en-1-one

Ahmad, N.; Siddiqui, H.L.; Zia-ur-Rehman, M.; Parvez, M.

doi:10.1107/S1600536810017150

Volume 66
Part 6
Pages o1346-o1347
June 2010

Received 9 May 2010
Accepted 10 May 2010
Online 15 May 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.026
wR = 0.073
Data-to-parameter ratio = 12.1
Details

(E)-3-(3-Chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one

Naveed Ahmad,^a Hamid Latif Siddiqui,^a Muhammad Zia-ur-Rehman ^b ^* and Masood Parvez ^c

^aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan,^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore-54600, Pakistan, and ^cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
Correspondence e-mail: rehman_pcsir@hotmail.com

The title molecule, C₁₆H₁₃ClO₂, is trans with respect to the C=C double bond. The dihedral angles between the mean plane of the prop-2-en-1-one unit and those of the 3-chloro- and 4-methoxy-substituted benzene rings are 20.93 (9) and 20.42 (10)°, respectively, and the dihedral angle between the mean planes of the two benzene rings is 40.96 (5)°. The crystal structure is stabilized by weak intermolecular C-HO hydrogen bonds, forming chains along the b axis.

Related literature

For the biological activity of chalcones, see: Dimmock et al. (1999); Opletalova & Sedivy (1999); Lin et al. (2002); Nowakowska (2007). For the synthesis and biological activity of related chalcone derivatives, see: Hussain et al. (2009). For non-linear optical studies of chalcones, see: Sarojini et al. (2006); Poornesh et al. (2009); Shettigar et al. (2006; 2008). For related structures, see: Rosli et al. (2006); Patil et al. (2006); Harrison et al. (2006); Fun et al. (2008); Jasinski et al. (2010).

Experimental

Crystal data

C₁₆H₁₃ClO₂
M_r = 272.71
Monoclinic, P 2₁
a = 10.3415 (6) Å
b = 3.8938 (1) Å
c = 16.9152 (10) Å
= 107.582 (2)°
V = 649.32 (6) Å³
Z = 2
Mo K radiation
= 0.29 mm^-1
T = 173 K
0.18 × 0.16 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997) T_min = 0.950, T_max = 0.989
2099 measured reflections
2099 independent reflections
2075 reflections with I > 2(I)

Refinement

R[F² > 2(F²)] = 0.026
wR(F²) = 0.073
S = 1.15
2099 reflections
173 parameters
1 restraint
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.14 e Å^-3
Absolute structure: Flack (1983), 687 Friedel pairs
Flack parameter: 0.08 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7AO2ⁱ	0.98	2.58	3.545 (2)	168
C16-H16O1ⁱⁱ	0.95	2.51	3.424 (2)	162
Symmetry codes: (i) x+1, y, z; (ii) x-1, y+1, z.

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5044 ).

Acknowledgements

The authors are grateful to the Institute of Chemistry, University of the Punjab, Lahore, and the PCSIR Laboratories Complex, Lahore, for the provision of necessary facilities.

References

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organic compounds